Dean x Reader On An Airplane
by horxruxes
Summary: You and Dean met on an airplane, and seemed to really hit it off.
1. Chapter 1

Your name: submit What is this?

You crammed into the tiny airplane seat sighing as you wished your company at least had splurged to upgrade for an extra inch or two. Adjusting your complimentary pillow trying to get comfortable you thought about how much you despised this part of your job. You hated flying the red-eye out of LAX to JFK, but I was one of the many "perks" of your job. Suddenly, a low voice startled you out of your thoughts.

"Is this seat taken?" The voice asked.

You looked up at the man with blonde hair, "Uh, no you can sit here," you replied moving your purse to the other side of your feet to make room.

The man put his suitcase in the overhead compartment, and squeezed into the tight chair next to you.

"I'm Dean, by the way," he said holding out his hand, looking into your eyes.

"I'm Y/N," you shook his hand noting his Irish green eyes.

"Nice to meet you Y/N," he replied with a smile.

You both turned your heads and stared straight ahead for a moment before your neighbor began, "Sorry, I feel like I'm bothering you. I'm just not the biggest fan of flying," he laughed nervously, "You'd think flying everywhere for my job would help that…"

You turned to look at him, "No, yeah, I totally understand."

"I should just become a pilot, I fly so much," he said light-heartedly.

"I hate flying the red-eye," you began,"And yet here I am every Thursday night flying the red-eye for meetings on Friday."

"You work out here in LA?" He asked

"Yeah, but there's another main office in Manhattan so I'm always flying out there."

"What do you?" He pressed.

"I work for a market research company, so I basically compile data for the companies that hire us. It's pretty boring." You looked into his eyes, and immediately looked away. His stare was so intense, but there was something intriguing about him. "What do you do?" You quickly asked.

"I'm a sales director at a company in New York, and they always send me out here to work with the other sales department…" he trailed off, and you both resumed staring at the back of the seats in front of you.

"What time is it?" You asked reaching down to grab your phone from your purse.

Dean checked his watch, "It's midnight, huh we were supposed to take of fifteen minutes ago…"

As if on cue, he was interrupted by the crackling on the pilot talking on the system, "I'm sorry folks, but we're going to be sitting here for awhile since there is an issue with the fuel system." The sound system crackled off.

"Oh good," Dean muttered rubbing his hands on his thighs.

"What?" You chuckled, "Nothing's gonna happen we're just sitting here." You reassured him.

"Yeah, but what if when we take off there is still an issue with…"

"OK, OK, just calm down, it's OK," You interjected, "Just breathe, it'll all be fine."

Dean let out a nervous laugh, "Thanks, I'm so bad with flying."

"It's OK. Just talk to me, you know, it'll… distract you." You said, smiling.

"OK…" He began.

It took the flight crews an hour to fix whatever issue there was with the plane, and in that time you learned more about Dean, and he learned more about you than you cared to admit.

The pilot came back onto the speaker to announce, "Ladies and gentleman, I'd like to announce that we will finally be taking off." A half-hearted, tired cheer went up among the crowd causing Dean to grab the armrests.

The plane started down the runway, and you rested your hand on his arm to calm him. Sometime in the five hour flight you fell asleep slumping your head on Dean's shoulder to his surprise.

At 6:00 AM you were shaken awake by your neighbor. Noticing the handsome man you had practically drooled on you shot up, and adjusted yourself apologizing the whole time.

"It's OK," he chuckled softly, "We just landed."

"Thanks," you shot him a smile, and immediately closed your mouth after sensing your bad breath.

He got up and grabbed his carry-on from the overhead, "I'll see you around then, it was nice getting to know you."

"Yeah you too," you replied. Sad to see him go, knowing you'd never see him again, but wanting to see him as quickly as he had gone.

You collected your things, left the airport, and hailed the nearest taxi to check into your hotel before your first meeting at 10:00 AM.

You arrived at the office building ten minutes early, and let the secretary know you were there. A few minutes later the head of your market research team emerged from the hallway.

"Y/N!' Your boss bellowed. You stood up and shook his hand.

"Hello, Mr. Roe. How are you?" You asked politely.

"Fine, I'm just fine. I hope you don't mind, but I had our meeting with the clients moved to a brunch spot just around the corner." He boomed.

"That's perfect, I'm pretty hungry from my flight."

You settled into your chair at the table after introducing yourself to the new clients.

"Y/N, here is one of our bests, and I think…" Your boss began before he was cut off by a low voice.

"Y/N?"

You glanced up at the source of the voice only to stare into bright, green eyes.


	2. Chapter 2

_You glanced up at the source of the voice only to stare into bright, green eyes._

"Dean?" You exclaimed in shock, and stood up out of your chair. Facing him you stare into his emerald eyes. After a moment you realized where you were, and turned to address the client and your boss, "I'm sorry, could you just excuse me one moment." You smiled at the client, who nodded as your boss looked on confused.

You pulled Dean aside to the bar in the upscale, Manhattan restaurant. "What are you doing?" You asked incredulously.

"Don't worry, sweetheart, I'm not stalking you. I'm here with an old friend of mine…"

"Well, I'm here with a client," you interrupted, "One I need to get back to."

Dean laughed and glanced down at his hands, you noticed how full his eyelashes were, and suddenly couldn't take you eyes off him, "Yeah, of course, you should get back to the meeting."

You turned to walk away muttering something like,"See you around". But Dean grabbed your arm, "Hey one thing though, maybe…. maybe we should meet up later, you know, gets some drinks…"

"I don't think so…" You started.

"Just one drink, with me, tonight," he pleaded.

You sighed, Dean was the kind of guy you stayed away from, but there was something about him… something you couldn't ignore.

"Alright," you huffed, and grabbed a napkin from the bar, and asked a passing waiter for a pen. You scribbled down your number, and slid it over to Dean, who was grinning proudly.

"I have to go now." You said starting to turn away from him.

"Yeah, see you soon, Y/N." He said after you glancing down at your phone number.

The entire meeting was a sham. You could feel Dean's gaze as you talked strategy with the client. At one point you made the mistake of glancing over at him which caused you to become flushed at his sly wink.

The meeting ended and you rushed out of the restaurant, not wanting to attract the unnerving attention of Dean. Your meetings were done for the day, and you went back to you hotel room to settle in and watch some _Real Housewives_ of some city. After pulling yourself out of you TV induced coma you ordered some take out. Halfway through your meal your phone sounded off. Some unknown number, but you answered it anyways.

"Hello?" You asked suspiciously.

"Hi, this Dean, from the plane." The voice said from the other side.

You smirked, he was nothing but persistent, "Hi, Dean," You said politely.

"So, I was wondering," he began, "if maybe you would like to get a drink with me… tonight?"

"Uh, yeah… I guess." You replied.

"Sounds good, I'll pick you up at 8 then?" He asked politely.

You agreed on the time and gave him the address of your hotel. Promising you'd have a good time with him, Dean said goodbye, and after the phone conversation you began to feel nervous. You tried laughing the nerves away, but it didn't help. Why were you even nervous, it was just drinks, yet there was something undeniable about Dean.

Before you knew it it was 8 o'clock, and you got a call from Dean letting you know he was down in the lobby. You met him in the lobby, and noticed how good he looked in a suit.

"Hey!" Dean cried when he saw you,

"Hi," you said quietly averting your eyes, hoping he didn't catch you staring.

"C'mon, I got a cab waiting outside." He led you outside, opened the door to the cab, and let you slide in.

Once in the cab he directed the driver to the bar.

"So, where are we going?" You asked breaking the silence.

"The best bar in the Upper East Side, you'll love it." He chuckled.

You got the feeling that this is where he took all of the people he flirted with on planes, but it didn't matter. You were excited just to be near him. He sent your blood pumping, and you couldn't figure out why you liked him so much.

At the bar Dean ordered a whiskey from himself and a martini for you. A few drinks later you were starting to feel a buzz, and the conversation turned to a flirtatious nature. Noting the time, you mentioned heading back to your hotel.

Dean led you outside and hailed a cab. He wrapped his arm around your waist, and your blood started racing. He helped you into the cab, and got in himself. Suddenly he was so close. You could smell the alcohol on him. You looked into his green eyes and the whole world was gone. All that mattered was Dean. How close he was. How he leaned in. How his lips gently brushed yours.

The cab screeched to a halt, and you were both jerked back into the reality of New York City. You looked into his eyes, and not wanting to leave his side you asked in a low voice, "Wanna come up?"

Dean nodded and payed the driver. You both got out of the cab and made your way into the hotel. In the elevator Dean's arm snaked around your waist pulling you closer to him. Once the elevator doors opened you broke free of his grasp and led him to your room.

Once in the room you threw your coat on the small couch, and headed for the kitchenette. "Do you want some coffee or something?" You asked.

Dean grabbed you and pulled you close to him, "Or something…" He whispered in your ear.

Your lips met again this time with so much intensity you had to sit down. On the couch Dean knotted his fingers in your hair, kissing you with ferocity. After what seemed like an eternity of kissing you adjusted your bodies to lay down on the couch. Dean's body hovered over yours as he began kissing down your neck, reveling in the pleasure. Instantly, you came to your senses and sat up.

"Y/N, what's wrong?" He asked in a gruff voice.

"Nothing…" You trailed off

Dean sensed your uneasiness stood up immediately, "I'm sorry," he said "I'll see myself out."

He grabbed his coat and waved awkwardly as he backed out of the door. You sat on the couch, head reeling from what happened, and fought the urge to run after him. What was wrong with you? Why were you so hooked on this guy you just met? Would you ever see him again?


	3. Chapter 3

You awoke to the drone of an alarm beeping. Turning over you could barely see the clock as it read, 9:00 AM. You turned onto your back and stared up at the ceiling. Before you knew it you were thinking about Dean. It was impossible to get him out of your head. Last night was the most amazing, yet confusing night of your life. The regret of kicking Dean out weighed heavily on your mind. You reached towards your nightstand feeling for your phone. The screen declared your lack of messages. Your heart sunk, since the moment you had woken up you hoped Dean would have called or texted you. You padded off to the bathroom to shower and hopefully forget about Dean….

Dean rolled over onto his side and checked his phone. Nothing. He opened up his contact list and scrolled to your name. He stared at your name unsure of whether or not to call. He tossed his phone onto the nightstand, and rolled over with a groan. Dean couldn't figure out why you had kicked him out last night. He couldn't keep you out of his mind, and it was driving him insane that he couldn't call you.

Once you were out of the shower in your bathrobe you shuffled around in your purse until you found an energy bar. Breakfast of Champions. You checked your phone again. _This is ridiculous_ , you thought, shut off your phone, and tossed it onto your bed.

After getting dressed you sat down on the couch only to remember last night, and move to sit on the bed, flicking on the TV. You were just about to settle in to watch whatever show was on until you heard a pounding at the door.

You walked over to the door, and slowly unlocked the it. You opened it, and found a nervous Dean. You ran your eyes over him; his hair was still wet like he just got out of the shower, he was only wearing a white T-shirt, jeans, and mismatched shoes.

Seeing your confusion Dean began, "I'm sorry, but I just had to talk to you," he paused, "I'm so sorry about last night, but just let me make it up to you. Come on a date with me…." he trailed off waiting for your response.

"Uhh, um… right now?" You asked pointing at his shoes.

Dean looked down at his outfit, "Right," he snapped his fingers and pointed at his shoes. Dean looked back up at you, "How about later tonight? 7 o'clock?"

"Uh, uh, yeah, yes, sure," you stammered.

"Sounds good," he said with a smile, "I'll pick you up at 7 then."

He stood awkwardly in the doorway for a moment then began to say, "I should go now."

At the same time you spoke up, "Do you want me to call a cab?"

He laughed a little, "No, I'll just go, see you later Y/N", he said stepping away from the door.

"Yeah, see you later," you waved awkwardly as he retreated down the hallway.

You shut the door and stood facing your hotel room. Dean was so confusing, but you were going out with him. And you had nothing to wear. You grabbed your suitcase, and threw it open, ruffling through your clothes. You sat down on the bed, frustrated, until you decided to get some food and go shopping. After ordering room service, and scarfing down the food you ordered, grabbed your purse, and flew out the door.

Dean couldn't stop smiling the whole ride home. He couldn't believe you were going out with him again, and he couldn't wait to see you dressed up for a date.

As soon as he got home he tossed himself onto the couch, and tried to drown you out of his thoughts with some mindless TV.

The first store was a bust, so was the second, and the third. As you walked into the fourth shop you vowed you would find something here. After at least an hour you found an outfit that was decent enough. Thanking the woman at the checkout counter you walked back to your hotel.

You had three more hours to kill until Dean came to pick you up, so you pulled up your laptop and began to look over some of your projects for work. Before you knew it you were Googling 'Dean Winchester'. You shut your laptop immediately, " _What the hell_ " you thought. You glanced over at the nightstand the clock read, 5:30.

After a few minutes you resolved to open your laptop and not stalk Dean. After half an hour you managed to get some work done without any cyberstalking, and decided to get ready.

You were finishing the last touches of your outfit when there was a knock on the door. Glancing in the mirror one last time you went to open the door.

"Hey, Dean! Come in." You said with a smile as he stepped into the hotel room. He looked good wearing a dark blue dress shirt with the sleeves rolled up to his elbows and black pants.

"So where are we going?" You asked grabbing your purse off the bed.

"There is this great little bistro-type place around the corner I thought we could go to…" he trailed.

You smiled, "Sounds great! Lead the way."

"Here let me get that for you," Dean said as he pulled out your chair for you.

You both sat in silence for a moment until the waiter came to take your orders. After ordering Dean spoke up, "Y/N, Listen I'm so sorry for what happened…"

You put your hand up to silence him, "It's OK. Let's just forget about that."

Dean smiled and chuckled, "Alright, sounds good."

After that you two were able to openly talk and the night no longer felt awkward. Once dessert time rolled around you excused yourself to the bathroom to "freshen up"

Staring at yourself in the mirror you could only think one thing, " _I'm falling for him._ " You shook the idea out of you head. What were you going to do anyways he lived here, and you lived in LA. This would never work, but he was still out there and you had to finish this date.

When you sat down at the table Dean began talking, "Have you ever been the the Empire State Building?"

You shook you head slowly.

"What?" he said in disbelief, "How have you never been to the Empire State Building? You know what this means, right? We're going."

"What? Now?" You began.

Dean waved over the waiter and asked for the check. "I'm taking you to the Empire State Building, and you are going to love it," he enunciated the last part as he signed the check.

Before you could say anything Dean was up, and getting ready to go. You shot to your feet as he turned on his heels to walk away.

"Hey! Wait up!" You cried after him, grabbing your jacket off the back of the chair.

Dean was waiting for you outside the restaurant on the sidewalk, "Ready?" He said in a low voice.

You nodded your head and stepped in stride with him. After a few steps Dean's arm snaked around your waist pulling you closer to him. You let out a quiet sigh reveling in his warmth.

The lobby of the building was almost empty with the occasional security guard strolling past. Dean paid the fee and the two of you headed towards the elevator. Inside the elevator you were alone with him, and you could feel how palpable the tension was between you two. Dean inched towards you, and pulled you close to him. You looked over at him and found his bright, emerald eyes looking deeply into yours. One of his gently calloused hands reached up to cup your cheek. Before you knew it his lips were crashing down onto yours, and he brought his other hand up to hold your face closer to his.

You could feel your heart pounding against your ribcage. Dean's lips were soft against your own, and he pulled away for half a second before gently kissing your jaw. You let out a small sigh of pleasure which cause him to pull away and smile while you blushed.

The elevator dinged to an end. You pulled away from Dean when the doors began to slide open adjusting your jacket, while Dean cleared his throat. Once the doors were fully open Dean offered you his hand, which you took and stepped out onto the outside top floor of the Empire State Building.

You and Dean walked to the edge of the observation deck. You stood there for a long time while Dean pointed out the different buildings in the skyline, even the building in the distance that he worked at. After walking around the deck holding hands, talking, and admiring the view, Dean offered to go visit Times Square, which you gleefully agreed to.

The traffic near Times Square was so bad Dean payed the cab driver and you both hopped out of the car and headed towards the lights. Dean pulled you closer to him as the crowds thickened in Times Square. You and Dean stood beneath the NBC Jumbotron as Dean wrapped his arms around you and tucked you closely into his chest.

Dean leaned down and whispered into your ear, "Do you wanna go back to my place, maybe?"

You knew it wasn't the best idea but you were tired of walking around, and just wanted to be somewhere private with him. You nodded in response

You looked up at the tall building as the taxi pulled up next to it. Dean led you to the elevator which you took up to the top floor. Once on the top floor you gasped, "You live in a penthouse?" you asked incredulously.

Dean chuckled, "Well I guess you could say I'm a playah," he said while unlocking the door.

You made a face, "Please, don't say that ever again."

He opened the door and motioned for you to enter. You smiled and gave him a nod as you stepped into his house.

You looked around the sleek and modernly furnished penthouse. Dean noticed your aghast stares, "What?" He asked laughing a little at your shocked look.

"Are you sure this is your house?" You replied, point at the giant wall of windows portraying the beautiful New York skyline, "We didn't just break into Hugh Hefner's New York home?"

"What? You don't believe me? I live here," he said in a convincing tone, "Look!" He pointed at a picture frame on the fireplace mantel.

You walked over to it and studied it closely. There was a picture of Dean laughing with another guy who had long, dark, brown hair. "Well, I guess you just lived in a crappy apartment, or gross motels." You said, still studying the picture. You heard Dean laughing in the background. "Who is this guy, anyways?" You asked, pointing to the picture.

Dean walked over to you, "That is my brother, Sam." He walked back to the open layout kitchen, "Do you want something to drink?"

"Yeah sure," you waved your hand behind you, "You never mentioned a brother…"

"What in the 48 hours we have known each other," Dean chuckled.

"Whatever," You said dully, turning around to see Dean holding two glasses of white wine. "Wine? Dean, you are an enigma…" You took the glass in his outstretched hand.

"I'll take that as a compliment." He tapped his glass against yours and took one big gulp. "How about some whiskey?"

You laughed, "OK, maybe you're not an enigma."

Dean turned around and walked to the mini bar and poured two whiskeys. You walked over and plopped down on the couch.

After a few more drinks you and Dean were laughing and sitting a little too close to each other for your own good. Dean was leaning in close, and you could smell the alcohol on his breath, but you couldn't help yourself. Before you knew it you were pressing your lips onto his.

Dean brought his hand up to the back of your head pushing you closer to him and not letting you leave his lips. Dean was slowly moving to lay down on the couch while you adjusted to straddle his hips, still locked in a kiss.

You pressed your hips down and felt his hardened, growing member as Dean let out a low groan.


	4. Chapter 4

There was light smell of bacon drifting through the air as you inhaled deeply. You stirred under the soft blanket draped over you, and slowly began to open your eyes. For half a moment you had no idea where you were until you looked up and saw Dean, dressed in pajama bottoms and a white t-shirt, standing at the stove in his kitchen softly humming as he flipped bacon.

You layed back down on the couch about to close your eyes once more when you realized that you were naked under the luxurious blanket. Immediately your eyes flew open and you looked down at the floor to see your clothes from last night entangled with Dean's clothes. You reached down and grabbed the first thing, Dean's dress shirt. While his back was to you you slipped out of the blanket and buttoned up Dean's shirt around you

"Good morning, sleepy head," Dean chuckled, "You look better than me in that shirt."

Dean turned back around to face the stove as you blushed, feeling exposed. You could see the muscles in his back rippling was he cooked, and you just wanted to feel his warm skin over his tight muscles. Dean began setting the island in the middle of his kitchen with plates stalked with breakfast food.

Slowly, you stood up and walked over to the island and sat down next to Dean who was already eating his food. You looked down at the food unable to eat.

"So…" You began, swallowing hard, "I'm going back home today… My plane is at 2:30," You looked over at the clock on the microwave, "Which is in three hours…"

Dean put down his fork and looked over at you, "All right, let's get you back to your hotel," Dean pushed his chair away from the table.

You grabbed his hand to stop him, "Dean, I don't want to leave, but I live in another state and I have go."

He looked over at out you through his eyelashes, "I know, so let's get you back to LA, right?"

You smiled as he got up and put the dishes in the sink, "I'm going to get dressed and you should do the same." Dean said smiling down at you. As he walked past he bent down and kiss you on the head.

After watching Dean walk down the hall to get dress you walked over to the pile of clothes by the coach, and slipped on your clothes. You sat down on the couch and thought about last night. All you could remember was Dean holding you close last night, and how it was one of the best nights….

"Hey! You ready?" Dean asked as he emerged from the hallway.

You got to your feet immediately shocked out of your reverie, "Yeah, let's go!" You cheered, trying to put enthusiasm in your voice.

The cab ride back to your apartment was silent, as you and Dean thought about what would happen in the next three hours. Once you arrived at your hotel you and Dean walked slowly down the hall until you reached your hotel room door.

"So… maybe I'll see you next time I'm in New York?" You asked quietly, glancing up at Dean.

"Yeah, or I could come see you in LA…" Dean trailed off and the two of you were left in silence.

After a long, pregnant pause Dean leaned down and pressed his lips to yours. His hand came up to cup your face as the kiss intensified. You could feel your heartbeat in your fingertips and brought your hand up to his neck, pushing his lips down on your harder.

Dean pulled his lips away from yours, "Wait, I'm sorry, we can't get into this again," Dean said in a low, gruff voice.

"I know," you said quietly, stepping back from him.

"OK, so… Have a safe flight back, and let me know when you're back in New York…" Dean started.

You stepped forward and kissed him lightly on his cheek shutting him up.

"Goodbye, Y/N." Dean leaned in and gave you a quick kiss on your forehead he then turned on his heel, and walked down the hallway until he turned the corner and was out of sight. You turned around and struggled to unlock your door as the tears started filling your eyes.

Thursday night and here you were again jammed into a tiny, uncomfortable, airplane chair. You were just about to put your headphones in when you heard a low voice, "Ma'am? Is this seat taken?"

You froze. You hadn't talked to him since the day you left New York, but... You glanced up only to find a middle-aged, balding man waiting for your answer.


End file.
